Potassium Iodide → 1-Fluoro-2-iodo-5-methyl-4-nitrobenzene

HRID 844213Notes

Reaction equation

HRID 844213 reaction equation
N([O-])=O.[Na+].[F:5][C:6]1[CH:12]=[C:11]([CH3:13])[C:10]([N+:14]([O-:16])=[O:15])=[CH:9][C:7]=1N.[I-:17].[K+]>O.Cl>[F:5][C:6]1[CH:12]=[C:11]([CH3:13])[C:10]([N+:14]([O-:16])=[O:15])=[CH:9][C:7]=1[I:17]

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 120999472-Fluoro-4-methyl-5-nitroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 226127641-Fluoro-2-iodo-5-methyl-4-nitrobenzene

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent3×

Procedure

A solution of sodium nitrite (3.6 g) in water (20 mL) was added dropwise over 10 min to a stirred suspension of 2-fluoro-4-methyl-5-nitroaniline (8.5 g, 50 mmol) in concentrated hydrochloric acid (100 mL) at 0° C. After a further 20 min at 0° C. the mixture-was added over 5 min to a solution of potassium iodide (9.1 g, 55 mmol) in water (30 mL) keeping the internal temperature below 20° C. After complete addition, the mixture was warmed to room temperature and stirred for 2 h then poured into water (500 mL) and extracted with ether (3×200 mL). The combined organic extracts were washed with saturated aqueous sodium thiosulfate solution (500 mL), dried (magnesium sulfate), filtered and concentrated in vacuo to leave the product as an orange oil. (400 MHz; CDCl3) δH 8.41 (1H, d, J 6 Hz), 7.02 (1H, d, J 8 Hz), 2.59 (3H, s); GC (25 m Quartz/Bonded Phase I; Injection Temperature 250° C.; Detector Temperature 320° C.; Temperature Ramp Rate: 100 to 320° C. at 10° C./min; Carrier Gas Helium; Flow Rate 12 mL/min) Retention Time: 5.92 min.

Workup

  1. customthe internal temperature below 20° C
  2. additionAfter complete addition
  3. extractionextracted with ether (3×200 mL)
  4. washThe combined organic extracts were washed with saturated aqueous sodium thiosulfate solution (500 mL)
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ca071ebeb2ea478d951190c9a6843660
Source dataset
uspto-grants-2002_04
Patent number
US06380238B1

Reaction notes

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